Daidzin

CAS# 552-66-9

Daidzin

Catalog No. BCN5891----Order now to get a substantial discount!

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Quality Control of Daidzin

Number of papers citing our products

Chemical structure

Daidzin

3D structure

Chemical Properties of Daidzin

Cas No. 552-66-9 SDF Download SDF
PubChem ID 107971 Appearance White powder
Formula C21H20O9 M.Wt 416.38
Type of Compound Flavonoids Storage Desiccate at -20°C
Synonyms Daidzoside; NPI-031D; Daidzein 7-O-glucoside
Solubility DMSO : ≥ 34 mg/mL (81.66 mM)
*"≥" means soluble, but saturation unknown.
Chemical Name 3-(4-hydroxyphenyl)-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one
SMILES C1=CC(=CC=C1C2=COC3=C(C2=O)C=CC(=C3)OC4C(C(C(C(O4)CO)O)O)O)O
Standard InChIKey KYQZWONCHDNPDP-QNDFHXLGSA-N
Standard InChI InChI=1S/C21H20O9/c22-8-16-18(25)19(26)20(27)21(30-16)29-12-5-6-13-15(7-12)28-9-14(17(13)24)10-1-3-11(23)4-2-10/h1-7,9,16,18-23,25-27H,8H2/t16-,18-,19+,20-,21-/m1/s1
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Source of Daidzin

1 Pueraria sp. 2 Trifolium sp.

Biological Activity of Daidzin

DescriptionDaidzin is a potent, selective aldehyde dehydrogenase 2 (ALDH2,IC50 = 80 nM) inhibitor, which has antiallergic anti-oxidant, anti-carcinogenic, antithrombotic,and anti-atherosclerotic activities, It has preventive effect on bone loss in ovariectomized rats appears to be due to suppression of bone turnover. A mixture of daidzin and glycitin has anti-obese and anti-diabetic effects.
TargetsIL Receptor | ALDH2
In vivo

Anti-obese and anti-diabetic effects of a mixture of daidzin and glycitin on C57BL/6J mice fed with a high-fat diet.[Pubmed: 25209298]

Biosci Biotechnol Biochem. 2015 Jan;79(1):117-23.


METHODS AND RESULTS:
We investigated the effects of a mixture of Daidzin and glycitin, which are the glycoside-form isoflavones of daidzein and glycitein, respectively, on body weight, lipid levels, diabetic markers, and metabolism in a high-fat diet (HF) fed C57BL/6J mice for 92 days. The mice were divided into basic diet group (CON), HF group, and HF companied with the isoflavone mixture group (HFISO). Results showed that mice in HFISO had a significantly lower body weight and adipose tissue compared to HF group. Blood glucose, serum HbA1c, and serum insulin also showed lower levels in HFISO group. In addition, higher hepatic GSH level and lower serum 8-hydroxy-2'-deoxyguanosine (8-OHdG) level were found in HFISO group mice.
CONCLUSIONS:
This suggests that the regulation of oxidative stress by Daidzin and glycitin was closely related to the suppression of adipose tissue and the progression of diabetes.

Pharmacological activation of aldehyde dehydrogenase 2 by Alda-1 reverses alcohol-induced hepatic steatosis and cell death in mice.[Pubmed: 25543082]

J Hepatol. 2014 Dec 24. pii: S0168-8278(14)00943-X.

Effective therapies for alcoholic liver disease are currently unavailable. The present study tested the efficacy of Alda-1, a specific aldehyde dehydrogenase 2 (ALDH2) activator, in treating alcoholic liver disease.
METHODS AND RESULTS:
Male C57BL/6J mice were exposed to alcohol for a time-course study on aldehyde metabolism. The specificity and efficacy of Alda-1 on activating hepatic ALDH2 and aldehyde clearance were determined by acute treatments. Then, mice were fed alcohol for 8 weeks with Alda-1 administration for the last 10 days to test the therapeutic potential of Alda-1. Lastly, H4IIEC3 cells were treated with ethanol, acetaldehyde, or 4-hydroxynonenal to define the link between aldehydes and hepatotoxicity. Alcohol feeding for 8 weeks induced hepatic ALDH2 dysfunction and aldehyde accumulation. One dose of Alda-1 administration elevated hepatic ALDH activity, which was blocked by the specific ALDH2 inhibitor, Daidzin. Alda-1 accelerated acetaldehyde clearance after acute alcohol intoxication. Alda-1 treatment in the 8-week alcohol feeding model reversed liver damage along with reduction of hepatic aldehydes. Alda-1 re-activated transcription factors, upregulated fatty acid oxidation enzymes, and reversed steatosis. Alcohol-induced endoplasmic reticulum stress and apoptotic cell death were also attenuated by Alda-1. Acetaldehyde or 4-hydroxynonenal treatment to H4IIEC3 cells inactivated transcription factors and induced endoplasmic reticulum stress and apoptosis, while ethanol per se showed limited effects.
CONCLUSIONS:
Pharmacological activation of ALDH2 by Alda-1 reversed alcoholic steatosis and apoptosis through accelerating aldehyde clearance. This study indicates that ALDH2 is a promising molecular target and Alda-1 has therapeutic potential for treating alcoholic liver disease.

Antithrombotic and antiallergic activities of daidzein, a metabolite of puerarin and daidzin produced by human intestinal microflora.[Pubmed: 12392089]

Biol Pharm Bull. 2002 Oct;25(10):1328-32.

To evaluate the antithrombotic activities of puerarin and Daidzin from the rhizome of Pueraria lobata, in vitro and ex vivo inhibitory activities of these compounds and their metabolite, daidzein, were measured. These compounds inhibited ADP- and collagen-induced platelet aggregation. Daidzein was the most potent. However, when puerarin and Daidzin were intraperitoneally administered, their antiaggregation activities were weaker than when these compounds were administered orally. When in vivo antithrombotic activities of these compounds against collagen and epinephrine were measured, these compounds showed significant protection from death due to pulmonary thrombosis in mice.
METHODS AND RESULTS:
To evaluate the antiallergic activity of puerarin, Daidzin, and daidzein, their inhibitory effects on the release of beta-hexosaminidase from RBL 2H3 cells and on the passive cutaneous anaphylaxis (PCA) reaction in mice were examined. Daidzein exhibited potent inhibitory activity on the beta-hexosaminidase release induced by DNP-BSA and potently inhibited the PCA reaction in rats. Daidzein administered intraperitoneally showed the strongest inhibitory activity and significantly inhibited the PCA reaction at doses of 25 and 50mg/kg with inhibitory activity of 37 and 73%, respectively. The inhibitory activity of intraperitoneally administered daidzein was stronger than those of intraperitoneally and orally administered puerarin and Daidzin.
CONCLUSIONS:
Therefore we believe that puerarin and Daidzin in the rhizome of Pueraria lobata are prodrugs, which have antiallergic and antithrombotic activities, produced by intestinal microflora.

Protocol of Daidzin

Cell Research

Identification of daidzein as a ligand of retinoic acid receptor that suppresses expression of matrix metalloproteinase-9 in HaCaT cells.[Pubmed: 23791815 ]

Mol Cell Endocrinol. 2013 Aug 25;376(1-2):107-13.

Cell lines:CV-1 cells
Concentrations:  0.5, 1, 10, 50, and 100 μM
Incubation Time:  24 h
Method:
CV-1 cells are transfected with 100 ng ERE-Luc and 50 ng ER-RARα or ER-RARγ. Transfected cells are treated with the indicated isoflavone at 0.5, 1, 10, 50, and 100 μM for 24 h. The β-Gal activity is used to normalize luciferase activity.

Animal Research

Preventive effects of the plant isoflavones, daidzin and genistin, on bone loss in ovariectomized rats fed a calcium-deficient diet.[Pubmed: 9477170]

Biol Pharm Bull. 1998 Jan;21(1):62-6.

Animal Models: Ovx rats
Formulation: 40% ethanol solution
Dosages:50 mg/kg/d for 4 weeks
Administration: p.o.

Daidzin Dilution Calculator

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Preparing Stock Solutions of Daidzin

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 2.4017 mL 12.0083 mL 24.0165 mL 48.033 mL 60.0413 mL
5 mM 0.4803 mL 2.4017 mL 4.8033 mL 9.6066 mL 12.0083 mL
10 mM 0.2402 mL 1.2008 mL 2.4017 mL 4.8033 mL 6.0041 mL
50 mM 0.048 mL 0.2402 mL 0.4803 mL 0.9607 mL 1.2008 mL
100 mM 0.024 mL 0.1201 mL 0.2402 mL 0.4803 mL 0.6004 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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References on Daidzin

Pharmacological activation of aldehyde dehydrogenase 2 by Alda-1 reverses alcohol-induced hepatic steatosis and cell death in mice.[Pubmed:25543082]

J Hepatol. 2015 Jun;62(6):1375-81.

BACKGROUND & AIMS: Effective therapies for alcoholic liver disease are currently unavailable. The present study tested the efficacy of Alda-1, a specific aldehyde dehydrogenase 2 (ALDH2) activator, in treating alcoholic liver disease. METHODS: Male C57BL/6J mice were exposed to alcohol for a time-course study on aldehyde metabolism. The specificity and efficacy of Alda-1 on activating hepatic ALDH2 and aldehyde clearance were determined by acute treatments. Then, mice were fed alcohol for 8 weeks with Alda-1 administration for the last 10 days to test the therapeutic potential of Alda-1. Lastly, H4IIEC3 cells were treated with ethanol, acetaldehyde, or 4-hydroxynonenal to define the link between aldehydes and hepatotoxicity. RESULTS: Alcohol feeding for 8 weeks induced hepatic ALDH2 dysfunction and aldehyde accumulation. One dose of Alda-1 administration elevated hepatic ALDH activity, which was blocked by the specific ALDH2 inhibitor, Daidzin. Alda-1 accelerated acetaldehyde clearance after acute alcohol intoxication. Alda-1 treatment in the 8-week alcohol feeding model reversed liver damage along with reduction of hepatic aldehydes. Alda-1 re-activated transcription factors, upregulated fatty acid oxidation enzymes, and reversed steatosis. Alcohol-induced endoplasmic reticulum stress and apoptotic cell death were also attenuated by Alda-1. Acetaldehyde or 4-hydroxynonenal treatment to H4IIEC3 cells inactivated transcription factors and induced endoplasmic reticulum stress and apoptosis, while ethanol per se showed limited effects. CONCLUSIONS: Pharmacological activation of ALDH2 by Alda-1 reversed alcoholic steatosis and apoptosis through accelerating aldehyde clearance. This study indicates that ALDH2 is a promising molecular target and Alda-1 has therapeutic potential for treating alcoholic liver disease.

Anti-obese and anti-diabetic effects of a mixture of daidzin and glycitin on C57BL/6J mice fed with a high-fat diet.[Pubmed:25209298]

Biosci Biotechnol Biochem. 2015;79(1):117-23.

We investigated the effects of a mixture of Daidzin and glycitin, which are the glycoside-form isoflavones of daidzein and glycitein, respectively, on body weight, lipid levels, diabetic markers, and metabolism in a high-fat diet (HF) fed C57BL/6J mice for 92 days. The mice were divided into basic diet group (CON), HF group, and HF companied with the isoflavone mixture group (HFISO). Results showed that mice in HFISO had a significantly lower body weight and adipose tissue compared to HF group. Blood glucose, serum HbA1c, and serum insulin also showed lower levels in HFISO group. In addition, higher hepatic GSH level and lower serum 8-hydroxy-2'-deoxyguanosine (8-OHdG) level were found in HFISO group mice. This suggests that the regulation of oxidative stress by Daidzin and glycitin was closely related to the suppression of adipose tissue and the progression of diabetes.

Description

Daidzin is an isoflavone that has anti-oxidant, anti-carcinogenic, and anti-atherosclerotic activities; directly inhibits mitochondrial aldehyde dehydrogenase 2 (IC50 = 80 nM) and is an effective anti-dipsotropic isoflavone.

Keywords:

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